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Erythromycin
Last updated: 18/05/2024
(Also known as: EES; abomacetin; abomacetin; erythromycin A)
GENERAL INFORMATION
Description
A macrolide antibiotic produced by Streptomyces erythreus and used in veterinary medicine
Availability status
Current
Introduction & key dates
1953, patented; 1968, first reviewed
Examples of veterinary uses
Used to treat a range of bacterial infections including mastitis, pneumonia, tick-borne infections like Lyme Disease, sinus infections, wound infections, skin infections, bone infections, and certain other types of bacterial infections
Examples of species treated
Poultry; Cattle; Sheep; Pigs
Approval status
VMR 2013/2033 approval status (GB/UK)
Approved
EU Regulatory approval status
Approved
Chemical structure
Isomerism
Isomeric
Chemical formula
C₃₇H₆₇NO₁₃
Canonical SMILES
CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O
Isomeric SMILES
CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O
International Chemical Identifier key (InChIKey)
ULGZDMOVFRHVEP-UMCXFAKASA-N
International Chemical Identifier (InChI)
InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19+,20+,21+,22-,23+,24-,25-,26+,28+,29+,30-,31+,32-,34-,35-,36-,37-/m1/s1
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
erythromycin B trihydrate Variant
erythromycin A dihydrate Variant
erythromycin B dihydrate Variant
erythromycin A -
General status
Veterinary substance type
Antibiotic, Antibacterial, Antimicrobial, Medicinal drug
Substance groups
Macrolide
Minimum active substance purity
-
Known relevant impurities
FAO: N-demethyl-erythromycin A; anhydroerythromycin A; erythromycin A enol ether; pseudoerythromycin A enol ether, erythromycin E, erythromycin F
Substance origin
Natural
Mode of action
Inhibits protein synthesis which is the basis of this antimicrobial action
Molecular targets
[3S rRNA, Antagonist], [50S ribosomal protein L22, Antagonist], [50S ribosomal protein L4, Antagonist]
CAS RN
114-07-8
EC number
204-040-1
CIPAC number
-
US EPA chemical code
-
PubChem CID
-
Therapeutic Class
Antiinfectants for systemic use: Antibacterials for intramammary use
ATCvet Code
QJ51FA01
Controlled Drug?
No
Regulation 37/2010 MRL Classification
Allowed substance (Table 1: All food producing species)
Molecular mass
733.93
PIN (Preferred Identification Name)
-
IUPAC name
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
CAS name
-
Other status information
-
Relevant Environmental Water Quality Standards
-
Physical state
White to slightly yellow crystalline solid, slightly hygroscopic
Related substances & organisms
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
Erythrocin 16.5% w/w soluble powder for oral solution Ceva Animal Health Ltd UK National authorisation (IC) Prescription only medicine to be authorised by a veterinarian (POM-V)
Formulation and application details
Often formulated as powders or oral use
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
2000
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
135
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
resolidifies MP(2) = 190		 -
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
3.02 X 1002 Calculated -
Log P
2.48
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
 Low
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
- - -
Dissociation constant pKa) at 25 °C
8.88
R4 R = Peer reviewed scientific publications
4 = Verified data
 -
@ 25DegC
Vapour pressure at 20 °C (mPa)
- - -
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
Volatilisation as max % of applied dose lost
From plant surface
- - -
From soil surface
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
pH 6.3: 280nm - -
Surface tension (mN m⁻¹)
- - -
Refractive Index
- - -
Environmental release
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
64
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 Moderately persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
USEPA data: >64 days in three soils - sandy clay loam, silty clay 7 silty loam
Manure DT₅₀ (days)
11
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Temp and OM dependent data for sandy loam+cattle manure 20°C		 -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
63.0
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 Moderately persistent
Note
at pH5 DT₅₀ 0.8 days; at pH9 DT₅₀ 35 days
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Air degradation
As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.
Decay in stored produce DT₅₀
-
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd (mL g⁻¹)
-
V1 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
1 = Estimated data with little or no verification
 Slightly mobile
Koc (mL g⁻¹)
570
Notes and range
Estimated
Freundlich
Kf (mL g⁻¹)
- - -
Kfoc (mL g⁻¹)
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
2.25 Calculated Transition state
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Known soil and groundwater metabolites

None

Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
des-N-methyl-erythromycin
Note: Major metabolite; Pharmacologically active		 - Humans (Liver) -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 4600
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Rat		 Low
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
- - -
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Soil micro-organisms
- - -
Collembola
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Non-target plants
- - -
- - -
Honeybees (Apis spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Chronic
- - -
Bumblebees (Bombus spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
-
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
-
Mason bees (Osmia spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Other bee species (1)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Other bee species (2)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Beneficial insects (Ladybirds)
- - -
Beneficial insects (Lacewings)
- - -
Beneficial insects (Parasitic wasps)
- - -
Beneficial insects (Predatory mites)
- - -
Beneficial insects (Ground beetles)
- - -
Aquatic ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
349
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Morone saxatilis		 Low
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
30.5
R4 R = Peer reviewed scientific publications
4 = Verified data
Daphnia magna		 Moderate
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
0.25
R4 R = Peer reviewed scientific publications
4 = Verified data
Daphnia magna		 Moderate
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
> 0.11
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Ceriodaphnia dubia		 Moderate
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)
- - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)
- - -
Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)
> 1000
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Lemna gibba as LOEC		 Low
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
0.02
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Pseudokirchneriella subcapitata		 Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
0.01
R4 R = Peer reviewed scientific publications
4 = Verified data
Selenastrum capricornutum		 Moderate
Mesocosm study data
NOEAEC mg l⁻¹
- - -
NOEAEC mg l⁻¹
- - -
Marine bivalves
- - -
HUMAN HEALTH AND PROTECTION
General
Property
Value
Source; quality score; and other information
Interpretation
Threshold of Toxicological Concern (Cramer Class)
High (class III) - -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 4600
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Rat		 Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
- - -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
Other Mammal toxicity endpoints
Subcutaneous LD₅₀ = 427 mg kg⁻¹
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat		 -
Intravenous LD₅₀ = 426 mg kg⁻¹
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Mouse		 -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
- - -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)
- - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)
- - -
Dermal penetration studies (%)
- - -
Dangerous Substances Directive 76/464
- - -
Exposure Routes
Public
-
Occupational
-
Mammalian dose elimination route and rate
Largely (~95%) metabolised by the liver and excreted in the bile and to lesser extent the urine
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
 -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
XNo, known not to cause a problem
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
XNo, known not to cause a problem
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
✓Yes, known to cause a problem
 No data found
?Possibly, status not identified
Respiratory tract irritant Skin irritant Skin sensitiser
?Possibly, status not identified
?Possibly, status not identified
 No data found
Eye irritant Phototoxicant  
✓Yes, known to cause a problem
 No data found  
General human health issues
May cause diarrhoea, nausea, abdominal pain, and vomiting
Reported cases of hearing impairment
Kidney, liver and lungs toxicant
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
-
WHO Classification
Not listed (Not listed)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
erythromycin
French
erythromycine
German
-
Danish
-
Italian
-
Spanish
eritromicina
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
Record last updated: 18/05/2024
Contact: aeru@herts.ac.uk
Please cite as: Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242